Podcast Summary: "Jeff Lewis Has Issues"

Episode: Caroline Rhea & Kym Whitley: Spying & Stolen Purses
Date: January 23, 2026
Host: Jeff Lewis (with recurring panel incl. Ryan Bailey, Shane, Sarah Colonna)
Guests: Caroline Rhea, Kym Whitley

Episode Overview

This lively episode of "Jeff Lewis Has Issues" brings together comedians and close friends Caroline Rhea and Kym Whitley for an unfiltered conversation packed with wild stories, hilarious banter, and candid insights into relationships, family, and personal quirks. Key themes include navigating co-parenting and single parenthood, the fun and mischief of female friendship, detective-level boyfriend spying, stolen (and gifted) luxury purses, and their shared history in standup and show business.

Key Discussion Points & Insights

1. TV and Pop Culture Hot Takes

[01:04–02:55]

• The crew opens with recommendations for reality TV—“The Valley,” “Traders,” “Landman”—and how reality shows offer both genuine conversation and delicious drama.
• Ryan Bailey offers glowing reviews:
  • "You have Gigi and her credit score... new characters you're actually fascinated by. So that's like a high recommend." – Ryan Bailey [02:18]

2. Friendships & Decades-Long Bonds

[06:03–16:23]

• Kym and Caroline dive in, immediately riffing on each other's outfits and playfully jabbing about a misinterpretation of the "Vegas showgirl" dress code.
• "I've known her for 30 years." – Kym Whitley [06:59]
• The pair have a long history, including Caroline attending Kym’s baby shower, co-parenting stories, and their time together in Hawaii (including a memorable, dolphin-induced pregnancy reveal).
• “Kim bathed Joshua, her son, in the sink at my house. That's how long we've known each other.” – Caroline Rhea [14:04]

3. Motherhood, Parenting, and Astrological Banter

[12:54–26:32]

• Caroline shares her struggles and joys with her 17-year-old daughter and discusses how mother-daughter relationships can feel like serving a “queen.”
  • “She is... I call her queen hormone. If she'll actually ever ask me to do anything, I'm thrilled. Her name for me is lady who fetches things.” – Caroline Rhea [22:12]
• Discussion about co-parenting, single parenting, and custody dynamics, both from Caroline’s and Jeff’s perspectives.
  • “It's very tricky when you divide like that. You have to be mother and father, both of you, each time.” – Caroline Rhea [25:51]
• Astrological signs are referenced throughout, using them to analyze personalities, compatibility, and even parenting styles.

4. Therapy, Relationships, and Life’s Unfiltered Messiness

[20:34–23:10]

• The comedians joke about therapy simply being “an hour of the day someone has to listen to you.”
  • “I started seeing a therapist because my family says I'm in denial, which is a total lie. And I've just convinced myself there's a friend I see once a week and then I lend her $220.” – Caroline Rhea [21:09]
• Caroline confesses to obsessing over exes, earning a therapist’s ultimatum.
  • “When your therapist says, ‘If you never mention him again, I won't charge you anymore.’” – Caroline Rhea [21:05]

5. Spying on Cheating Boyfriends: Kym’s PI Adventures

[27:11–30:33]

• Kym details her “spy” era, including using spyware and even physical stakeouts to catch a cheating fiancé.
  • “There’s some real joy in being able to spy on someone. It gets to be fun. It's wrong, you know?” – Caroline Rhea [29:04]
  • “I had a camera in a tissue box. I had a lot of stuff going on. I was doing too much.” – Kym Whitley [29:17]
• The moral tangle and adrenaline of “catching” a partner is hilariously dissected—both admit the process becomes its own twisted entertainment.

6. Stolen (and Gifted) Purses, Storage Units, and the Sisterhood of Stuff

[33:47–44:05]

• Kym tells the saga of discovering Caroline accidentally gifted her a valuable Gucci purse, and the confusion (and jokes) that follow when Caroline demands it back to give to her sister.
  • “Three weeks ago, my niece is like, ‘Caroline gave you a Gucci?’…I went in the little zipper part because it was brand new…and the little zipper part had the paperwork and everything. I was like, she gave me a Gucci. I was like, she loves me.” – Kym Whitley [40:48]
  • “Parallel universe…I'm like, where is the Gucci purse I bought my sister? I cannot find this purse.” – Caroline Rhea [41:27]
• The duo riff on their histories of swapping clothes and possessions, accidentally mixing up valuable items, and what it reveals about their friendship.
• Caroline's storage unit is sold off after a payment mix-up, leading to surprising relief even as sentimental items are lost.
  • “Honestly, a little part of me was relieved. One storage unit down.” – Caroline Rhea [38:55]

7. Collecting, Curating, and Sentimental Hoarding

[44:14–45:31]

• Caroline reveals a vast teacup collection rooted in her mother’s influence and a dream of someday opening a tea house as a remedy for social isolation.
  • “I went into an antique store…I was like Patrick Swayze in Ghost. My mother went into my body and started picking teacups.” – Caroline Rhea [44:33]
  • Dream: “One day to have, like, a big, open tea house where strangers...can start chatting.” – Caroline Rhea [44:58]
• Kym claims “collector” status, especially of “panties and gadgets,” leading to a running joke on excessive possessions.

8. Dating Younger Men and Ageing in Hollywood

[48:06–49:22]

• Caroline, in classic self-deprecating fashion, jokes about "dating younger men" (who aren't even that young).
  • “You know you’re old when the younger man you’re dating is old.” – Caroline Rhea [48:06]
  • "It's not that younger men are interested in me... the man I'm dating is in his 40s. This is not robbing the cradle!" – Caroline Rhea [48:06]
• Anecdotes about her first (cluelessly gay) boyfriend and her mother's dry wit.
  • “Darling, Gary is here. And darling, I think the R is silent.” – Caroline Rhea, quoting her mother [49:18]

9. Promotions, Stand-Up, and Upcoming Shows

[19:53, 46:19–47:34]

• The Ice House show in Pasadena, upcoming Vegas double bill, and Caroline’s special “I Identify as a Witch.”
  • For tickets: veeps.com/carolineray [$11.99] [46:54]
• The pair tease more comedy collaborations in the works, and the communal magic that happens when they perform together.

Notable Quotes & Memorable Moments

• “Her name for me is lady who fetches things.” – Caroline Rhea [22:12]
• “I had a camera in a tissue box. I had a lot of stuff going on. I was doing too much.” – Kym Whitley [29:17]
• “You know you’re old when the younger man you’re dating is old.” – Caroline Rhea [48:06]
• “My mother goes, darling, it’s not like 39 is young. What's the problem?” – Caroline Rhea [48:31]
• Caroline’s dolphin impression [16:04] causes uproarious laughter, and her “useless skills” become a running gag.
• Banter about showgirl outfits devolves into whether Caroline looks “classy” or “expensive,” with jokes about high-end sex work [06:39].
• The group joyously inducts the guests into “chump” status (the show's inside joke and fanbase moniker) [34:24].

Important Timestamps

• Spying/boyfriend cheating story: [27:11–30:33]
• Stolen purse saga: [40:06–42:30]
• Parenting/kids discussion: [22:12–26:32]
• Teacup collecting & loneliness anecdote: [44:33–45:31]
• Comedy dates & promo details: [19:53, 46:19–47:34]
• Mother-daughter banter/"lady who fetches things": [22:12]
• Dolphin impersonation segment: [16:04]

Conclusion

This episode is vintage “Jeff Lewis Has Issues”: a winning mix of candid confession, acerbic wit, and authentic connection. Caroline and Kym shine as real-life friends who have weathered Hollywood and heartache together—trading laughter, misadventures, and designer handbags with equal parts affection and sharp tongue. For fans of unfiltered conversation, this one is as entertaining and warm as it gets.

For more from Jeff Lewis and guests, catch live shows on SiriusXM or the Jeff Lewis Channel. For upcoming stand-up dates and tickets, see veeps.com/carolineray or check listings for The Ice House and Jimmy Kimmel’s in Vegas.